A series of compounds having benzofuran ring structure has excellent antiparasitic activity and antiinsect activity. Among them, avermectin and milbemycin are now practically used. Four components, α, β, γ and δ, of nemadectin, which has benzofuran ring structure produced by Streptomyces cyaneogriseus subspecies noncyanogenus, are known, and the C-13 position thereof has no substituent and is saturated as shown in the following structure.

Nemadectin α R1═H R2═CH(CH3)2 
Nemadectin β R1═H R2═CH3 
Nemadectin γ R1═CH3 R2═CH3 
Nemadectin δ R1═CH3 R2═CH(CH3)2 
A reason why the C-13 position of nemadectin is saturated is that a module 7 of nemadectin polyketide synthetase (nemadectin PKS), which is involved in the formation of nemadectin aglycon moiety, is constructed by the structure of KS-AT-DH-ER-KR-ACP. It is difficult to construct stereoselective modification in the saturated C-13 position by chemical synthesis. Although increasing antiinsect activity and antiparasitic activity can be expected by an addition of sugar moiety as like in avermectin of the following structure, a production of derivatives by chemical synthesis has not been made.

As described in the above, although stereoselective introduction of hydroxyl group and glycosylation of the hydroxyl group of nemadectin at C-13 position by chemical synthesis might be difficult to perform, as a result of extensive studies, we have succeeded in preparing C-13 glycosylated nemadectin producing microorganism by means of the molecular genetic technology and obtaining efficiently nemadectin with stereoselective glycosylation.
The present invention was completed based on such the knowledge. An object of the present invention is to provide a microorganism belonging to genus Streptomyces having C-13 glycosylnemadectin producing activity by the molecular genetic technology. Another object of the present invention is to provide a microorganism strain belonging to genus Streptomyces having C13 substituted nemadectin producing activity, which can be used for obtaining effectively nemadectin with stereoselective glycosylation and expected to improve the biological activity thereof.
Further object of the present invention is to provide a method for manufacturing C-13 substituted nemadectin comprising introducing DNA of a microorganism, which produces nemadectin analog, into the nemadectin producing microorganism belonging to genus Streptomyces and accumulating C-13 hydroxylnemadectin and C-13 glycosylnemadectin and collecting the same.